Chloroacetic Acid → Benzoic acid, 2-(carboxymethoxy)-

HRID 2097112Notes

Reaction equation

HRID 2097112 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[Na+].Cl[CH2:14][C:15]([OH:17])=[O:16]>O>[C:15]([CH2:14][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 338Salicylic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 69461Benzoic acid, 2-(carboxymethoxy)-Yield 24%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of salicylic acid (20 g, 145 mmol) in water (200 mL) is added carefully sodium hydroxide (60 g, 1.45 mol) followed by chloroacetic acid (27 g, 290 mmol). The mixture is refluxed for 5 d, cooled to room temperature and the precipitate is filtered and dried. Trituration with hexanes yielded the title compound (6.84 g, 24%) as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ 7.65-7.66 (dd, 1H, J=8.0, 2.0 Hz), 7.45-7.47 (dd, 1H, J=8.0, 2.0 Hz), 6.97-7.05 (m, 2H), 4.77 (s, 2H).

Workup

  1. temperatureThe mixture is refluxed for 5 d
  2. filtrationthe precipitate is filtered
  3. customdried

Sources & evidence

ORD record
ord-e5efc8f5bfaf453b9b7c10df2c742ca6
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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